AZIRIDINYL KETONES AND THEIR CYCLIC ANILS. 9.* SUBSTITUTED 1,3-DIAZABICYCLO[3.1.0]HEX-3-ENES Z. Kaluski, A. Gresyak-Figas, N, P. Vorob'eva, A. I. Bakumenko, F. G. Yaremenko, and V. D. Orlov UDC were obtained by the reaction of a,8-dibromodihydrochalcones with ammonia and formaldehyde (or acetone). Their structures were confirmed by spectral methods and x-ray diffraction analysis.
The interest in substituted 1,3-diazabicyclo[3.1.0~hex-3-enes is due to their photochromic properties [2][3][4][5]. It has been proposed that compounds with a p-nitrophenyl group in the 6 position of the two-ring system, for which the most profound changes in color are characteristic, be used to obtain light-sensitive materials, including materials for recording photographic and holographic images [6][7][8][9][10][11]. In the present research we set out to study the structure and the effect of various substituents on the properties of 1,3-diazabicyclo[3. 1.0]hex-3-ene.
The method for the synthesis of the desired heterocycle proposed in [2,6] was based on the reaction of aldehydes (or ketones) and ammonia with aziridinyl ketones II, which, in turn, are obtained from =,8-dibromodihydrochalcones I. The process can be accomplished in one step without isolation of aziridinyl ketones II; to obtain high yields ammonia should be passed into a suspension of dibromide I in methanol until the dibromide has dissolved completely, and the aldehyde or acetone should be added to the reaction system only after this while continuing saturation of the solution with ammonia: H N 4-R ~ C6H4 ~'~" CCC6H4R2-4 II ~'~/-" ~N~ -,-r~co NH~ + R~CO 4_RI C6H. CHDrC|[B~ CC C~ if4 R2_4 -__ 4-RI C6H4--~ I a-k R~/"-R~